Piperazine → N,N'-bis[(5,6,7-trimethoxynaphthalen-2-yl)methyl]piperazine

HRID 987412Notes

Reaction equation

HRID 987412 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[C:9]=2[O:13][CH3:14])[CH:4]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[C:25](=[O:28])([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:13][C:9]1[C:8]([O:15][CH3:16])=[C:7]([O:17][CH3:18])[CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][C:3]([CH2:2][N:19]1[CH2:24][CH2:23][N:22]([CH2:2][C:3]3[CH:12]=[CH:11][C:10]4[C:5](=[CH:6][C:7]([O:28][CH3:25])=[C:8]([O:15][CH3:16])[C:9]=4[O:13][CH3:14])[CH:4]=3)[CH2:21][CH2:20]1)=[CH:4]2

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 218916422-Chloromethyl-5,6,7-trimethoxynaphthalene

Product 1

HCID 12108580N,N'-bis[(5,6,7-trimethoxynaphthalen-2-yl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloromethyl-5,6,7-trimethoxynaphthalene (418 mg) and piperazine (63 mg) were dissolved in DMF (10 mL), potassium carbonate (207 mL) was added to the solution, and the mixture was stirred at room temperature for 5 hours. After concentrating the reaction mixture under reduced pressure, chloroform was added to the residue, and the mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=40:1) to obtain the title compound as a free base.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure, chloroform
  2. additionwas added to the residue
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-49a2a0c6e99e42748b7126b071638a59
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

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